Classifications

• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q5/00—Preparations for care of the hair
  • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
  • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
  • A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
  • A61K8/8152—Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
  • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
  • C08F220/10—Esters
  • C08F220/12—Esters of monohydric alcohols or phenols
  • C08F220/14—Methyl esters, e.g. methyl (meth)acrylate
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
  • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
  • C08F220/10—Esters
  • C08F220/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
  • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10S526/00—Synthetic resins or natural rubbers -- part of the class 520 series
  • Y10S526/923—Ethylenic monomers containing at least one salt group

Definitions

• the present invention concerns new copolymers, a process of preparing said copolymers and cosmetic compositions containing them, in particular lacquers and waving lotions.
• compositions for the hair such as lacquers and waving lotions.
• polymers containing functions of quaternized tertiary amines such as those described in the French Pat. No. 72 32244, polymers resulting from the copolymerization of methyl methacrylate, methacrylate of quaternized dimethylaminoethyl, and octadecyl methacrylate.
• Polymers of this type are proven to present a good affinity for hair but they lack brilliance and good mechanical properties. Furthermore, they are not easily compatible with certain propulsive agents used in lacquers.
• copolymers of the invention are indeed endowed with excellent solubility in ethanol and hydroethanolic mixtures; moreover, they exhibit good compatibility with propulsive agents used in the aerosol industry.
• the present invention has for its purpose some copolymers in which at least three constituent monomers have a methacrylic structure wherein the copolymers correspond to the following general formula: ##STR3## where: B represents Na, K, NH 4 , or ##STR4## R 1 and R 2 , identical or different, represent an atom of hydrogen or the radical--(X--OH;
• X represents an alkylene radical, branched or unbranched, having from 1 to 3 carbon atoms or an alkylene radical, branched or unbranched, substituted by at least one hydroxymethyl;
• M represents at least one typical unsaturated monomer of the group consisting of: the acrylamides or methacrylamides substituted on the nitrogen by an alkyl radical, branched or unbranched, the acrylates
• X is from 22% to 64% in moles
• y is from 13% to 73% in moles
• z is from 6% to 23% in moles; and v is from 0% to 22% in moles;
• the acrylamides or methacrylamides substituted on the nitrogen by a branched or unbranched alkyl radical correspond to the following formula: ##STR5## where: R 3 , R 4 , and R 5 , identical or different, represent either a hydrogen atom or a methyl radical; and
• R 6 is an alkyl radical, branched or unbranched, having from 1 to 11 carbon atoms.
• the acrylates or methacrylates of monoalkylether of ethylene of polyethylene glycol correspond to the following formula: ##STR6## where: R 3 has the same significance as in formula II;
• R 7 represents a methyl or ethyl radical
• n is an integer between 1 and 12.
• organic or inorganic bases susceptible of leading to embodiments of formula Ia of the copolymer of formula I of the invention one can cite the following: sodium hydroxide, potassium hydroxide, ammonium hydroxide, and amino-alcohols including monoethanolamine; diethanolamine; triethanolamine; isopropanolamine; diisopropanolamine; tri(hydroxy-2propyl-1) amine, sold under the trade name of "tri-isopropanolamine” by Ugine-Kuhlman Co.; amino-2 methyl-2 propanol-1; amino-2 methyl-2 propanediol-1,3; and amino-2 hydroxymethyl-2 propanediol-1,3.
• sodium hydroxide, potassium hydroxide, ammonium hydroxide, and amino-alcohols including monoethanolamine; diethanolamine; triethanolamine; isopropanolamine; diisopropanolamine; tri(hydroxy-2propyl-1) amine, sold under the trade name of "tri-isopropanol
• the copolymer of the invention have molecular weights between 10,000 and 1,500,000, and usually between 15,000 and 200,000.
• an object of the present invention consists of the process of preparation of the new copolymers of the invention.
• the copolymers of the invention have been obtained in working out for the first time the copolymerization of a mixture (i) of N,N-dimethylamino-2 ethyl methacrylate, (ii) methyl methacrylate, (iii) methacrylic acid, and (iv) possibly at least one other monomer corresponding to the radical M, and in then neutralizing the free carboxylic acid functions of the copolymer with the aid of an organic or inorganic base chosen among those mentioned above.
• This procedure is completely suitable, particularly when the base is an inorganic base like sodium hydroxide, potassium hydroxide, or ammonium hydroxide.
• the copolymers of the invention can be obtained by copolymerizing a mixture of (i) N,N-dimethylamino-2 ethyl methacrylate; (ii) methyl methacrylate; (iii) methacrylic acid in its salt form, e.g., by reaction with an amino-alcohol of the formula: ##STR7## where: R 1 , R 2 , and X have the same significance as previously; and (iv) possibly at least one other monomer corresponding to the radical M.
• This reaction is performed preferably in an organic solvent such as ethyl ether or alcohol at an ambient temperature 0° C. to 20° C.
• the latter is then copolymerized in the presence of other monomers.
• ammonium methacrylates of formula V can be cited in particular: the methacrylate of (hydroxy-1 methyl-2) propyl-2 ammonium, the methacrylate of (dihydroxy-1,3 methyl-2) propyl-2 ammonium, and the methacrylate of tri((hydroxy-2) propyl-1) ammonium.
• This process of copolymerization in which the methacrylic acid is made to occur in the salt form is particularly advantageous when one desires to obtain a copolymer no longer containing any free carboxylic acid function.
• the copolymerization itself is performed with classical methods, i.e., in solution in a solvent, either in mass, or even in suspension in an inert liquid, or in an emulsion.
• a further procedure includes polymerization by precipitation which consists in using a solvent in which the monomers are soluble but in which the polymers precipitate. According to this process the polymer is isolated by filtration.
• the solvents appropriate for this type of polymerization include cyclohexane, methylethylketone, heptane, ethyl acetate, etc.
• the catalysts used are generators of free radicals such as azo-bis-isobutyronitrile, peresters, or oxidation-reduction systems.
• peresters can be mentioned in particular tertiobutyl ethyl-2 perhexanoate and tertiobutyl perpivalate.
• oxidation-reduction systems one can cite in particular the aqueous couples of oxygenated ferrous chloride, persulfate of ferrous ammonium chloride, etc.
• the quantity of catalyst generally comprises between 0.1% and 6% by total weight of the monomers used for copolymerizing.
• copolymerization can likewise be brought about or simply activated by means of irradiation.
• the copolymerization reaction is generally performed by heating under nitrogen and agitation at a temperature about 55° C. to 85° C.
• the duration of heating is preferably between 6 and 24 hours.
• the solvent is preferably an alcohol, and especially ethanol.
• the present invention similarly has for its object, new industrial products based on a cosmetic composition containing from 0.5% to 10% by weight at least of a copolymer of formula I and in the form of a lacquer or a waving lotion, or again in the form of a shampoo, a tint, or of a treatment lotion applied before or after shampooing or tinting.
• Waving lotions of the invention present themselves in the form of aqueous or hydroalcoholic solutions containing from 20% to 70% alcohol and have a concentration of copolymer comprising between 1% and 3% by weight.
• the alcohols generally used for such waving lotions are preferably lower aliphatic alcohols of low molecular weight, such as ethanol or isopropanol.
• waving lotions can in addition contain diverse adjuncts such as plastifiers, perfumes, and colorings.
• the lacquers for the hair of the invention are obtained by placing in solution in an alcohol at least one copolymer as defined previously, this solution being placed in an aerosol bomb and mixed with a propellant agent.
• the copolymer is generally present in a proportion comprising between 0.5% and 10% by weight.
• the lacquers likewise can contain a third-part solvent that can be present in a proportion between 3% and 35% by weight.
• the alcohol which can be either ethanol or isopropanol, generally is present in a propellant between 5% and 80%, and preferably between 6% and 69.5% by weight.
• the third-part solvents that can be used in the lacquers one can cite in particular methylene chloride, trichloroethane, ethyl chloride, acetone, ethyl acetate, and dichlorodifluoroethane.
• propellant agents one can use fluorochloric hydrocarbons either alone or in a mixtire such as that known under the trade name of Freon; in particular, Freon 11, 12, 22, and 142b.
• fluorochloric hydrocarbons either alone or in a mixtire such as that known under the trade name of Freon; in particular, Freon 11, 12, 22, and 142b.
• propellant agent carbon dioxide or nitrous oxide, or hydrocarbons such as propane, butane, isobutane, etc., these propulsants being used either alone or mixed together, or with one or several Freon mixtures such as those mentioned above.
• the Freons are employed in combination with carbon dioxide or nitrous oxide.
• the copolymers of formula I similarly can be used in compositions of the invention in association with other polymers of anionic or cationic character, the compositions appearing then in the form of creams, gels, emulsions, etc.
• the polymer with anionic or cationic character is present in the composition at a concentration between 0.01% and 10%, and preferably between 0.02% and 5%.
• compositions of the invention can contain, or course, in addition, other ingredients such as those generally used in cosmetics, such as plastifiers, brilliantines, perfumes, colorings, restructuring agents, and some anionic, cationic, or non-ionic massaging agents.
• other ingredients such as those generally used in cosmetics, such as plastifiers, brilliantines, perfumes, colorings, restructuring agents, and some anionic, cationic, or non-ionic massaging agents.
• the present invention has for its object a process for waving hair. According to this procedure, one applies on the hair at least one waving lotion such as described above before rolling the hair on waving rollers (of diameter 15 to 30 mm), and one then submits the hair to drying (at temperatures of the order of 25° C. to 55° C.).
• the amount applied to the hair depends on the volume of the head, but is generally of the order of 10 to 100 cm 3 , and preferably of the order of 20 to 50 cm 3 .
• the polymer obtained presents a viscosity of 1.90 cp in 5% solution in DMF at 34.6° C.
• This polymer similarly has been obtained according to the procedure described in example Ib above my proceeding with the copolymerization of: 20 g (0.2 mole) of methyl methacrylate, 62 g (0.395 mole) of N,N-dimethylamino-2 ethyl methacrylate, and 18 g (0.103 mole) of (hydroxy-1 methyl-2) propyl-2 ammonium methacrylate.
• the copolymer obtained shows a viscosity of 2.00 cp in 5% solution in DMF at 34.6° C.
• the copolymer obtained is soluble in absolute ethanol. Viscosity: 2.35 cp in 5% solution in DMF at 34.6° C.
• the polymer obtained shows a viscosity of 2.07 cp in 5% solution in dimethylformamide (DMF) at 34.6° C.
• one describes the preparation of a copolymer of the invention by the process consisting of a first period of preparing the polymer in free-acid form, and of a second period of neutralizing the carboxylic acid functions by an organic or inorganic base.
• the copolymer is obtained with a quantitative yield. Viscosity: 2.02 cp in 5% solution in DMF at 34.6° C.
• the copolymer thus obtained shows a viscosity of 1.78 cp in 5% solution in dimethylformamide at 34.6° C.
• copolymer obtained according to this example can be used directly in ethanol solution for the embodiment of cosmetic compositions using this solvent as medium.
• One prepares according to the invention a shampoo by mixing the following ingredients:
• the shampoo is left in contact with the hair for 15 minutes before rinsing, making the hair bright and soft to the touch.
• One prepares according to the invention a shampoo by mixing the following ingredients:

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Cited By (65)

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Citations (4)

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• 1978
  • 1978-04-18 US US05/897,435 patent/US4237253A/en not_active Expired - Lifetime
  • 1978-04-20 BR BR7802490A patent/BR7802490A/pt unknown
  • 1978-04-20 CH CH426878A patent/CH630648A5/fr not_active IP Right Cessation
  • 1978-04-20 DE DE19782817369 patent/DE2817369A1/de not_active Withdrawn
  • 1978-04-20 GB GB15722/78A patent/GB1596875A/en not_active Expired
  • 1978-04-20 CA CA000301544A patent/CA1116348A/fr not_active Expired
  • 1978-04-20 NL NL7804234A patent/NL7804234A/xx active Search and Examination
  • 1978-04-20 IT IT7867901A patent/IT7867901A0/it unknown
  • 1978-04-21 JP JP4675078A patent/JPS53132091A/ja active Pending
• 1980
  • 1980-06-25 US US06/162,927 patent/US4324780A/en not_active Expired - Lifetime

Patent Citations (4)

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